1H-Indazol-6-amine → HCID 10267798, compound

HRID 1595789Notes

Reaction equation

HRID 1595789 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]#[N:15].[NH2:16][C:17]1[CH:25]=[C:24]2[C:20]([CH:21]=[N:22][NH:23]2)=[CH:19][CH:18]=1.Cl.N1C=CC=CC=1>C(OCCO)C>[NH:23]1[C:24]2[C:20](=[CH:19][CH:18]=[C:17]([NH:16][C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][C:3]=3[C:14]#[N:15])[CH:25]=2)[CH:21]=[N:22]1

Participants

5

Reactant 3

HCID 814231H-Indazol-6-amineHCID 10176127Pyridinium chlorideHCID 224667634-Chloro-6-methoxy-quinoline-3-carbonitrile

Product 1

HCID 10267798HCID 10267798, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

To a suspension of 218.6 mg (1.0 mmol) of 4-chloro-6-methoxy-3-quinolinecarbonitrile and 159.8 mg (1.2 mmol) of 6-aminoindazole in 10 mL of 2-ethoxyethanol was added 115.6 mg (1.0 mmol) of pyridine hydrochloride. The resulting reaction mixture was refluxed for 1 hr. After cooling, most of solvent was evaporated off and the residue was diluted with ether. The precipitate was collected by filtration and was taken into water. The aqueous suspension was neutralized to PH 7-8 by addition of sat. sodium carbonate aqueous solution and stirred for 15 min. The separated solid was filtered off and washed with water and ether. After drying in vacuo, 297.5 mg (94.3%) of the product was obtained as a deep yellow solid, m.p.>250° C., mass (electrospray, m/e): M+H 315.8. HRCIMS m/z: cacld 315.112 for C18H13N5O (M+), obsd 315.1124

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 1 hr
  3. temperatureAfter cooling, most of solvent
  4. customwas evaporated off
  5. additionthe residue was diluted with ether
  6. filtrationThe precipitate was collected by filtration
  7. additionThe aqueous suspension was neutralized to PH 7-8 by addition of sat. sodium carbonate aqueous solution
  8. filtrationThe separated solid was filtered off
  9. washwashed with water and ether
  10. customAfter drying in vacuo

Sources & evidence

ORD record
ord-4f65732363ff48b19c774db9f666f313
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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